Methyl iodide → HCID 59627221, compound

HRID 1523246Notes

Reaction equation

HRID 1523246 reaction equation
[H-].[Na+].[CH2:3]([C@:6]1([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:11][CH2:10][N:9]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH3:13])[C:8](=[O:21])[NH:7]1)[CH:4]=[CH2:5].[CH3:29]I>C1COCC1>[CH2:3]([C@:6]1([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:11][CH2:10][N:9]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH3:13])[C:8](=[O:21])[N:7]1[CH3:29])[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59627209HCID 59627209, compound

Product 1

HCID 59627221HCID 59627221, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (84 mg, 2.1 mmol) in THF (1 mL) was added a solution of (R)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one (50 mg, 0.120 mmol) in THF (5 mL) at 0° C. The resulting mixture was stirred for 2 h. Then CH3I (50 mg, 0.35 mmol) was added. The mixture was stirred for 3 h. The reaction was quenched with satd aq NH4Cl. The organic phase was separated, and concentrated to give the crude product, which was purified by preparative TLC to afford (R)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-3-methyltetrahydropyrimidin-2(1H)-one (11.7 mg, 23%). LC-MS Method 1 tR=1.403 min, m/z=431; 1H NMR (CDCl3): δ=1.38 (d, 3H), 1.63 (m, 1H), 2.19 (m, 2H), 2.70 (m, 2H), 2.83 (m, 3H), 5.20 (m, 2H), 5.71-5.84 (m, 2H), 6.91 (m, 2H), 7.05 (m, 4H), 7.32 (m, 2H).

Workup

  1. stirringThe mixture was stirred for 3 h
  2. customThe reaction was quenched with satd aq NH4Cl
  3. customThe organic phase was separated
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-f339cc3b35624961974039e2aff45462
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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